Herbicidal pyridinsulfonamides

ABSTRACT

N-[(5-Substituted pyrimidin-2-yl)aminocarbonyl]-2-haalopyridine-3-sulfonamides are useful as herbicides.

RELATED APPLICATION

This application is a continuation-in-part of my copending applicationU.S. Ser. No. 059,152, filed July 20, 1979, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to N-(5-substitutedpyrimidin-2-ylaminocarbonyl)sulfonamides and their use as agriculturalchemicals.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H,halogen, CF₃ or alkyl.

Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR2## wherein R is butyl, phenyl or ##STR3## R₁ is hydrogen ormethyl. When tested for hypoglyemic effect in rats (oral doses of 25mg/100 g), the compounds in which R is butyl and phenyl were mostpotent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR4##

Based upon similarity to a known compound, the author predictedhypoglycemic activity for the foregoing compound.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (i), and their use as general orselective herbicides. ##STR5## wherein R₁ and R₂ may independently bealkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

Compounds of Formula (ii), and their use as antidiabetic agents, arereported in J. Drug. Res. 6, 123 (1974). ##STR6## wherein R is pyridyl.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodneeds, such as soybeans, wheat and the like. The current populationexplosion and concomitant world food shortage demand improvements in theefficiency of producing these crops. Prevention or minimizing the lossof a portion of such valuable crops by killing, or inhibiting the growthof undesired vegetation is one way of improving this efficiency.

A wide variety of materials useful for killing, or inhibiting(controlling) the growth of undesired vegetation is available; suchmaterials are commonly referred to as herbicides. The need exists,however, for still more effective herbicides that destroy or retardweeds.

SUMMARY OF THE INVENTION

According to this invention, there is provided compounds of Formula Iand their agriculturally suitable salts, suitable agriculturalcompositions containing them, and methods of using them as selective, aswell as general herbicides having both pre-emergence and post-emergenceactivity. These compounds are highly active herbicides. Compounds whereR₂ =H are useful as intermediates to highly active herbicides. ##STR7##wherein A is ##STR8## B is Cl or Br; R is CO₂ R², ##STR9## SO₂ NR³ R⁴,Cl, CF₃, NO₂ or S(O)_(n) R³ where n is 0, 1 or 2;

R¹ is H, Cl, F, Br, NO₂, CH₃, OCH₃ or CF₃ ;

R² is H, C₁ -C₆ alkyl, C₃ -C₄ alkenyl, C₂ -C₃ haloalkyl, C₅ -C₆cycloalkyl, C₄ -C₇ cycloalkylalkyl, CH₂ OCH₂ CH₂ OCH₃, CH₂ -CH(CH₃)OR⁵or (CH₂)_(m) OR⁵ where m is 1, 2 or 3;

R_(a) ² is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl or OCH₃ ;

R_(b) ² is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl or R_(a) ² and R_(b) ² can betaken together to form --CH₂ --₅, --CH₂ --₄ or --CH₂ CH₂ -O-CH₂ CH₂ --;

R_(c) ² is C₁ -C₄ alkyl or C₃ -C₄ alkenyl;

R³ is C₁ -C₄ alkyl or OCH₃ ;

R⁴ is C₁ -C₄ alkyl;

R⁵ is C₁ -C₃ alkyl;

X and Z are independently H, CH₃, Br, Cl, OCH₃, CH₂ CH₃, CH₂ OCH₃ orOCH₂ CH₃ ; and

Y is F, Cl, Br, I, CH₃, CH₂ CH₃, CH₂ CH₂ CH₃, (CH₂)₃ CH₃, CH₂ -CH═CH₂,OCH₃, OCH₂ CH₃, CN, CH₂ CH₂ Cl, CH₂ CH₂ CH₂ Cl, CH₂ CH₂ OCH₃, OCH₂ OCH₃,CH₂ OCH₃, OCH₂ CH₂ OCH₃, CH₂ CO₂ R⁶, CH₂ CH₂ CO₂ R⁶, CO₂ R⁶, ##STR10##or NO; R⁶ is CH₃ or CH₂ CH₃ ;

and their agriculturally suitable salts; provided that:

(1) when R_(a) ² is OCH₃, then R_(b) ² is CH₃ ;

(2) when R³ is OCH₃, then R⁴ is CH₃ ; and

(3) when R is Cl, then Y is F.

Preferred for reasons of higher herbicidal activity, or ease insynthesis, or both are:

(1) those compounds of Formula I, wherein R is CO₂ R² or SO₂ NR₃ R₄.

(2) those compounds of Formula I, wherein R¹ is H.

More preferred for reasons of even higher herbicidal activity or morefavorable ease of synthesis, or both, are:

(3) those compounds of Preferred (1) wherein R¹ is H.

(4) those compounds of the More Preferred (3) wherein R² is C₁ -C₄alkyl, C₃ -C₄ alkenyl, or C₂ -C₃ haloalkyl, and Y is F, Cl, Br, CH₃, C₂H₅ or CH₂ CH₂ Cl, and at least one of X or Z is CH₃, OCH₃, Et or OEt.

Most preferred for their yet even higher herbicidal activity or evenmore favorable ease of synthesis, or both are:

(5) those compounds of the More Preferred (4), wherein X is H, CH₃ orOCH₃ and Y is F, Cl, Br, CH₃, C₂ H₅ or CH₂ CH₂ Cl.

Specifically preferred for highest herbicidal activity, or mostfavorable ease of synthesis, or both are:

Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate;

Methyl2-{[(4-chloro-6-methoxy-5-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoate;

Methyl2-[[[4-chloro-5-(2-chloroethyl)-6-methylpyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoate;

Methyl2-[[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl2-[[(5-iodo-4,6-dimethylpyridimin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl2-[[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl2-[[(5-bromo-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl2-[[(5-ethyl-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-Chloro-N-[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide;

Methyl2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzoate;

(2-Propenyl)2-[[(5-fluoro-4,6-dimethoxypyrimidin-2-yl)aminocarbonyl[aminosulfonyl]benzoate;

Methyl2-[[(5-chloro-4-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;and

Methyl2-[[(5-ethyl-4-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.

DETAILED DESCRIPTION Synthesis

As shown in Equation 1, below, the compounds of Formula I can beprepared by the reaction of an appropriate 2-aminopyrimidine of FormulaII with an appropriately substituted benzenesulfonyl isocyanate ofFormula III; R being equal to CO₂ R², SO₂ NR³ R⁴, Cl, CF₃, NO₂ orS(O)_(n) R³ where n=0 or 2 and R₁, X, Y and Z being as previouslydefined above. ##STR11##

The reaction is best carried out in inert aprotic solvents such asmethylene chloride, acetonitrile or tetrahydrofuran at ambienttemperature. The mode of addition is not critical; however, it is oftenconvenient to add the sulfonyl isocyanate to a stirred suspension of theaminopyrimidine since the isocyanates are usually liquids or low meltingsolids and their addition is more easily controlled. The reaction isgenerally mildly exothermic. In some cases, the desired product issoluble in the warm reaction medium and crystallizes from it in pureform on cooling. Products soluble in the reaction mixture are isolatedby evaporation of the solvent, trituration of the solid residue withsolvents such as 1-chlorobutane ethyl ether or pentane and filtration.

The intermediate sulfonyl isocyanates of Formula III can be prepared byreacting corresponding sulfonamides with phosgene in the presence ofn-butyl isocyanate at reflux in a solvent such as chlorobenzene,according to the procedure of H. Ulrich and A. A. Y. Sayigh, NewerMethods of Preparative Organic Chemistry, Vol. VI p 223-241, AcademicPress, New York and London, W. Foerst Ed. In cases where formation ofthe desired sulfonyl isocyanate is difficult by the above procedure thesulfonylurea formed by reaction of butyl isocyanate with the appropriatesulfonamide is treated with phosgene according to the above reference.

Benzenesulfonyl isocyanates with o-alkoxycarbonyl and o-sulfamoylsubstituents are novel. These are prepared according to Equation 2.##STR12##

A mixture of the appropriate sulfonamide, e.g. an o-alkoxycarbonylbenzenesulfonamide IV such as the methyl ester, which is known in theart, an alkyl isocyanate such as butyl isocyanate and a catalytic amountof 1,4-diaza[2,2,2]bicyclooctane (DABCO) in xylene or other inertsolvent of sufficiently high boiling point (e.g. >135°) is heated toapproximately 135°. Phosgene is added to the mixture until an excess ofphosgene is present as indicated by a drop in the boiling point. Themixture is heated further to drive off the excess phosgene. After themixture is cooled and filtered to remove a small amount of insolubleby-products, the solvent and alkyl isocyanate are distilled off in-vacuoleaving a residue which is the crude sulfonyl isocyanate IIIa.

The novel pyridinesulfonyl isocyanates can also be prepared by theprocedure of Equation 2 by substituting the appropriate 2-chloro orbromo pyridine sulfonamide for the o-alkoxycarbonyl benzenesulfonamideIV shown above.

The preparation of sulfonamides from ammonium hydroxide and sulfonylchlorides is widely reported in the literature, e.g. Crossley et al., J.Am. Chem. Soc. 60, 2223 (1938).

Certain sulfonyl chlorides are best prepared by chlorosulfonation of asubstituted benzene or thiophene according to the teaching of H. T.Clarke et al. Org. Synth. Coll. Vol. 1, 2nd Ed. 1941, p. 85. Otherbenzenesulfonyl chlorides are best made by diazotization of theappropriate aniline with sodium nitrite in HCl as taught by H. L. Yaleand F. Sowinski, J. Org. Chem. 25, 1824 (1960).

Compounds of Formula V can be prepared by reacting appropriatelysubstituted 2-aminopyrimidines of Formula II with2-halo-3-pyridinesulfonyl isocyanates, Formula VI (B=Br, Cl) as shown inEquation 3. ##STR13##

Compounds of Formula Ia, where R is equal to ##STR14## can be preparedfrom the N-(pyrimidin-2-yl)-2-methoxycarbonylbenzenesulfonamides (VIII)of this invention by treatment with dimethylaluminum amines as shown inEquation 4. ##STR15##

The intermediate alkylaminoaluminum compounds prepared according to A.Basha, M. Lipton and S. W. Weinreb, Tetrahedron Letters 4171 (1977), aremixed with a suspension of the esters in toluene or similar inertsolvent and the mixture is refluxed for one to six hours. The productcan be isolated by evaporation of the solvent toluene, adding methylenechloride and aqueous hydrochloric acid to decompose the residualreaction mass and extracting the desired product into methylenechloride. Evaporation of the methylene chloride yields the desiredproduct in sufficiently pure form for the purpose of this invention.

Compounds of Formula Ib, where R is equal to ##STR16## can be preparedfrom the N-(pyrimidin-2-yl)-2-methoxybenzenesulfonamide VIII, of thisinvention by treatment with dimethylaluminum alkylthiolates as shown inEquation 5. ##STR17##

The intermediate aluminum thiolates can be prepared according to R. P.Hatch and S. W. Weinreb, Journal of Organic Chemistry, Vol. 42, 3960(1977). The reaction of the thiolate with the ester of this invention isbest carried out in a neutral solvent such as toluene or xylene atreflux for one to three hours. Best results are obtained when thealuminum thiolate compound is present in excess of the stoichiometricamount required.

Compounds of Formula Id, where R is equal to SOR³ can be prepared fromthe appropriate compounds of Formula Ic where R is equal to SR³ ; R, X,Y and Z being as previously defined, by oxidation withm-chloroperbenzoic acid according to Equation 6. ##STR18##

The reaction can be carried out by stirring equivalent amounts of Icwith m-chloroperbenzoic acid in an inert solvent such as chloroform andstirring at 0° C. to reflux for 12-24 hours after which the insolublem-chlorobenzoic acid produced is removed by filtration and thechloroform solution containing the desired sulfoxide is concentrated toyield the crude product. The product can be purified further bydissolving it in aqueous base of pH 10 and adjusting the pH to 4 toprecipitate the desired compound while leaving the m-chlorobenzoic acidin solution as its sodium salt.

Compounds of Formula Ie, wherein R² is -H, can be prepared by hydrolysisof esters of Formula VIII wherein R² is C₁ -C₆ alkyl. As shown inEquation 7, alkali metal base catalyzed hydrolysis in aqueous methanolproduces the alkali metal carboxylate from which the carboxylic acid isobtained by treatment with mineral acids such as HCl: ##STR19##

The reaction of Equation 7 is best carried out in a solution containingthe compound being hydrolyzed, 2 to 10 parts of methanol, 10-50 parts ofwater and 2-10 equivalents of a base such as sodium or potassiumhydroxide maintaining the temperature at 15°-90° C. for 3-24 hours. Thereaction yields the soluble alkali metal salt of the carboxylic acid,which is suitable for the purposes of this invention. Conversion ofthese salts to the acid form is easily carried out by addition to thereaction medium of strong mineral acids, such as hydrochloric orsulfuric acid, causing the desired carboxylic acids to precipitate fromsolution.

Compounds wherein R² is H can be converted to compounds of thisinvention where R² is a higher alkyl or substituted hydrocarbyl group,as already disclosed herein, by the reaction of salts of the parent acid(R² =H) with R² -Halogen as shown in Equation 8. ##STR20##

The reaction of Equation 8 is of use where the intermediate compound R²-Halogen contains a readily replaceable halogen as is the case forsubstituted or unsubstituted allylic halides, or alkoxyalkyl halides.

The procedure of Equation 8 is best carried out in inert polar solventssuch as tetrahydrofuran, acetonitrile or acetone by combining theappropriately substituted carboxylic acid and base such as triethylamineor 1,4-diaza[2,2,2]bicyclooctane adding the appropriate halide andheating the mixture to reflux with stirring for 1 to 16 hours. Thereaction mixture can be evaporated to dryness and the residue trituratedwith water, filtered and washed with water to separate the desiredproduct from the water soluble salt.

Certain compounds of Formula I, where R² -Halogen is less reactive, aremore conveniently prepared by reaction of the silver salt of thecarboxylic acid and the appropriate R² -Halogen. The reaction is carriedout in a suitable solvent such as acetonitrile between 0° and 80° for1-6 hours and the product is isolated as described above.

The synthesis of heterocyclic amine derivatives has been reviewed in"The Chemistry of Heterocyclic Compounds", a series published byInterscience Publ., New York and London. 2-Aminopyrimidines aredescribed by D. J. Brown in "The Pyrimidines", Vol. XVI of the aboveseries.

The principal synthesis of 5-substituted 2-aminopyrimidines is carriedout by reacting guanidine with suitably substituted β-dicarbonylcompounds such as β-diketones, β-aldehydoketones, malonic esters, andβ-ketoesters. Preparation of 5-halogen-2-aminopyrimidines with N-halogensuccinimide has been taught by T. Wishiwaki, Tetrahedron 22, 2401(1966).

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by treating compounds of Formula I witha solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g. hydroxide, alkoxide, carbonate orhydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by directtreatment of an aqueous solution of a salt of a compound of Formula I(e.g. alkali or quaternary amine salt) with a solution containing thecation to be exchanged. This method is most effective when the desiredsalt containing the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g. an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged. In this method, the cation of the resin isexchanged for that of the original salt and the desired product iseluted from the column. This method is particularly useful when thedesired salt is water-soluble.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centrigrade and parts are by weight unless otherwise designated.

EXAMPLE 1 Methyl 2-(isocyanatosulfonyl)benzoate

A stirred mixture containing 157 g of methyl 2-sulfamoylbenzoate, 73 gof butyl isocyanate, 0.3 g of 1,4-diazabicyclo[2,2,2]octane and 1.0 l ofxylene was heated to reflux for one half hour. Phosgene gas was thenpassed into the system under a dry ice reflux condenser allowing thereaction temperature to drop to 120°. This addition was continued untilthe reflux temperature remained at 120° without further phosgeneaddition. The temperature of the reaction mixture was then raised to136° (by removal of the dry ice reflux condenser) after which it wascooled to room temperature and filtered. Evaporation of the filtrateyielded the desired crude sulfonyl isocyanate which could be purified bydistillation at 132°-138° C. under 1.0 to 1.1 mm of mercury pressure.The product is extremely reactive with water so contact with moistureshould be scrupulously avoided.

EXAMPLE 2 Isopropyl 2-(isocyanatosulfonyl)benzoate

To 60.7 g (0.25 mole) of isopropyl 2-sulfamoylbenzoate in 300 ml dry(molecular sieves) xylenes was added 25.0 g (0.25 mole) N-butylisocyanate and 0.1 g 1,4-diazabicyclo[2,2,2]octane. The mixture washeated to reflux temperature and phosgene was slowly bubbled through thesolution for two hours.

An infrared spectrum of the reaction mixture indicated formation of thedesired sulfonyl isocyanate (2250 cm⁻¹). The resulting cloudy solutionwas cooled to room temperature and decanted from a small amount of solidimpurity. Evaporation of the resulting clear solution yielded thedesired crude sulfonyl isocyanate, which was used in subsequent stepswithout further purification.

EXAMPLE 3 Methyl2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]-aminosulfonyl}benzoate

2-Amino-5-chloropyrimidine (1.3 g) was suspended in 20 ml of methylenechloride and to this was added with stirring 2.4 g of methyl2-(isocyanatosulfonyl)-benzoate. After stirring for three hours atambient temperature, the desired product,2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid,methyl ester, which had precipitated as a white solid, was filtered off.It melted at 217°-221° and showed peaks in the nuclear magneticresonance spectrum (trifluoroacetic acid solvent) at 4.0δ (singlet) forOCH₃, 9.0δ for H at the 4- and 6-position of the hetero ring and at 7.9δand 8.2-8.4δ for aromatic H, consistent for the above-named product.

EXAMPLE 4 Methyl2-{[(4-chloro-6-methoxy-5-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate

To 1.0 g of 2-amino-4-chloro-6-methoxy-5-methylpyrimidine in 35 ml ofanhydrous acetonitrile, with stirring at ambient temperature, was added1.5 g of methyl 2-(isocyanatosulfonyl)benzoate. The mixture was stirredfor 3 hours, heated to 50° and allowed to cool. The solid precipitatethus obtained was filtered off and washed with 1-chlorobutane. It meltedat 204°-205° and showed infrared absorption peaks at 1740, 1710, 1650and 1510 cm⁻¹, consistent for the above-named product.

EXAMPLE 5 Methyl2-{[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-aminosulfonyl}benzoate

To a mixture of 1.0 gram (0.0073 mole) of2-amino-4,5,6-trimethylpyrimidine and 5.0 ml of dried methylene chloridestirring magnetically in a 50 ml RB single neck flask, 2.1 grams ofmethyl 2-(isocyanatosulfonyl)benzoate was added at room temperature andthe mixture stirred at room temperature for 24 hours. Butyl chloride (4ml) was added with constant stirring and the insoluble product filtered,washed immediately with butyl chloride and dried. (Yield 1.3 grams, m.p.152°-161°). IR (Nujol): 5.60, 5.75 (C═O), 11.25 11.90 microns; NMR(TFA-d): δ2.30 (s,3H,CH₃), 2.65 (s, 6H, 2CH₃), 4.00 (s, 3H, CO₂ CH₃),7.60-8.60 (m, ArH).

EXAMPLE 6N-[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonylbenzenesulfonamide

To 4.1 g ofN[(4,5,6-trimethylpyrimidin-2-yl)-2-methoxycarbonyl]benzenesulfonamidein 75 ml of toluene is added 37 ml of a methylene chloride and toluenesolution (3:5) containing 1.25 g of dimethylaluminum dimethylamide withstirring at ambient temperature. The mixture is heated to reflux (82°C.) for two hours, cooled, 10 ml of methanol added and the solventsevaporated in vacuo. The residue is treated with a mixture of methanol,water and dilute hydrochloric acid and the precipitate is filtered offto yield the desired product.

EXAMPLE 7N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-(methylthio)carbonylbenzenesulfonamide

Trimethylaluminum (6.0 ml, 2 M) is charged via syringe to 15 ml drytoluene under nitrogen atmosphere and 3.8 gN-[(5-chloro-4,6-dimethylpyrimidin-2-yl)-aminocarbonyl]-2-methoxycarbonylbenzenesulfonamideis added portionwise. After stirring at room temperature for one hour,methyl mercaptan (gas) is passed through the reaction mixture until theinitial temperature rise subsided, whereupon the addition isdiscontinued. The reaction mixture is allowed to stir at roomtemperature for 1 hour, and quenched with 25 ml of 10% HCl. Theresultant white suspension is filtered to give the desired product.

EXAMPLE 8 N,N-Diethyl-1,2-benzenedisulfonamide

To a solution of 114 g of o-amino-N,N-diethylbenzenesulfonamide in amixture of 400 ml of concentrated hydrochloric acid and 100 ml ofglacial acetic acid was added a solution of 50 g of sodium nitrite in130 ml of water at -5° to 0°. The solution was stirred at 0° for 15minutes then poured into a mixture of 14 g of cuprous chloride and 100ml of liquid sulfur dioxide in 550 ml of glacial acetic acid at 0°-5°.This mixture was stirred at 0° for 15 minutes then at room temperaturefor 3 hours before pouring into three liters of ice water. The crudesulfonyl chloride was filtered off and washed with water. It was thendissolved in 1 l of ethyl ether, washed with water and dried overmagnesium sulfate. To this ether solution was added 20 ml of liquidanhydrous ammonia at 5°-15°. After stirring overnight at roomtemperature the solid was filtered off, washed with water, ethanol andthen 1-chlorobutane. Oven drying at 60° gave 91.8 gN,N-diethyl-1,2-benzenedisulfonamide, m.p. 156°-9°.

NMR(DMSO-d₆) δ: 0.9-1.2 [t, 6.0H, (CH₃ CH₂)₂ N-1; 3.2-3.6 [qt, 3.8H,(CH₃ CH₂)₂ N-]; ˜7.2 [broad singlet 2.1H, NH₂); 7.7-8.4 (m, 4.1H, 4aromatics).

EXAMPLE 9 O-N,N-Diethylsulfamoylbenzenesulfonyl isocyanate

A solution of 13.2 g of N,N,diethyl-1,2-benzenedisulfonamide, 4.5 g ofn-butylisocyanate, and 0.2 g of 1,4-diaza[2,2,2]bicyclooctane (DABCO) in90 ml of mixed xylenes was heated to 135°. To this solution was added3.3 ml of liquid phosgene at such a rate that the temperature wasmaintained between 125° and 135° (about 2 hours). The temperature waskept at 130° for 1/2 hour after the addition. The solution was cooledand filtered to remove a small amount of insoluble solid thenconcentrated at 60°-70° in-vacuo. The residue ofo-N,N-diethylsulfamoylbenzenesulfonyl isocyanate was an oil weighing16.8 g and was sufficiently pure for further reaction.

EXAMPLE 10N,N-Diethyl-N'-[(4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide

A mixture of 0.8 g of 2-amino-4,5,6-trimethylpyrimidine, 2.8 g of thecrude sulfonyl isocyanate from Example 9 and a few crystals of DABCO in25 ml of acetonitrile is stirred at room temperature for 16 hours. Asmall amount of unreacted aminopyrimidine is filtered off and thefiltrate concentrated in-vacuo to give a hard glass. Crystallizationfrom methanol givesN,N-diethyl-N'[4,5,6-trimethylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamideas a white solid.

EXAMPLE 11 2-Chloro-3-pyridinesulfonylisocyanate

To 125 ml of dry xylene was added with stirring 20.7 g of2-chloro-N-(butylcarbamoyl)-3-pyridinesulfonamide. This solution washeated to reflux, and phosgene added until no further uptake of this gaswas observed. It was then cooled, filtered and the solvent removed invacuo to yield 2-chloro-3-pyridinesulfonylisocyanate as an oil Bp108°-110° (0.7 mm Hg) and showing a sharp absorption peak in theinfrared region at 2220 cm⁻¹.

EXAMPLE 122-Chloro-N-[(5-chloro-4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

To a stirred suspension of 1.4 g of2-amino-5-chloro-5,6-dimethylpyrimidine in 20 ml of dry acetonitrile atroom temperature is added 2.2 g of2-chloropyridine-3-sulfonylisocyanate. The mixture is stirred forseveral hours, evaporated to dryness and the residue is mixed with 30 mlof water and enough 10% sodium hydroxide to adjust the pH to 11. Thismixture is filtered and the filtrate adjusted to pH 7 by the addition of10% hydrochloric acid and then refiltered. Acidification of thisfiltrate to pH 2 causes the desired compound to precipitate. The desiredcompound is filtered off and dried.

By using the procedures of Examples 3-7, 10 and 12, with equivalentamounts of the appropriate aminopyrimidine and the appropriatelysubstituted sulfonyl isocyanate, the compounds in Tables I and II can beprepared.

Alternatively, the methods of Examples 3-6 are used to obtain compoundswhere R is equal to SOR³, ##STR21##

                                      TABLE I                                     __________________________________________________________________________    R              R.sub.1                                                                            X     Y        Z     m.p. (°C.)                    __________________________________________________________________________    CO.sub.2 CH.sub.3                                                                            H    H     Br       H     200-204°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Br       CH.sub.3                                                                            152-155°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           Br       OCH.sub.3                                                                           190-195°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                                                            158-161°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Br       OCH.sub.3                                                                           180-183°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           Cl       CH.sub.3                                                                            165-170°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Cl       CH.sub.3                                                                            170-174°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           Cl       OCH.sub.3                                                                           186-190°                      CO.sub.2 CH.sub.3                                                                            H    Cl    Cl       CH.sub.3                                                                            172-174°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           CH.sub.3 CH.sub.3                                                                            197-198°                      CO.sub.2 CH.sub.3                                                                            H    H     CH.sub.3 OCH.sub.3                                                                           185-193°                      CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CH.sub.2 Cl                                                                   CH.sub.3                                                                            193-196°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                           218-219°                      CO.sub.2 CH.sub.3                                                                            H    Cl    C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                           157-158°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            126-129°                      CO.sub.2 CH.sub.3                                                                            H    Cl    C.sub.2 H.sub.5                                                                        CH.sub.3                                                                            188-189°                      CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.3 CH.sub.3                                                                            186-189°                      CO.sub.2 CH.sub.3                                                                            H    H     Br       CH.sub.3                                                                            202-203°                      CO.sub.2 CH.sub.3                                                                            H    Cl    Br       Cl    201-202°                      CO.sub.2 CH.sub.3                                                                            H    H     Cl       CH.sub.3                                                                            199-202°                      CO.sub.2 CH.sub.3                                                                            H    Cl    Cl       Cl    209-211°                      CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           CH.sub.2 CH.sub.2 OCH.sub.3                                                            CH.sub.3                                                                            135-140°                      CO.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                           H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.2 OCH.sub.3                                                                  H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                                                        H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3                                               H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                          Cl    187-189°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                      H     168-170°                      CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                                                            200-202°                      CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    CH.sub.3                                                                            Cl       CH.sub.3                                                                            218-220°                      CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H    CH.sub.3                                                                            Cl       CH.sub.3                                                                            181-183°                      CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                                                            112-114°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            I        CH.sub.3                                                                            198-201°                      CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CHCH.sub.2                                                                    Cl    142-145°                      CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    H     Br       CH.sub.3                                                                            164-170°                      CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    CH.sub.3                                                                            I        CH.sub.3                                                                            177-182°                      NO.sub.2       H    CH.sub.3                                                                            Cl       CH.sub.3                                                                            180-190°                      NO.sub.2       H    H     Cl       CH.sub.3                                                                            232-237°                      NO.sub.2       H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                                                            190-200°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                    CH.sub.3                                                                            143-149°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            n-butyl  CH.sub.3                                                                            170-175°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3 C.sub.2 H.sub.5                                                                     175-183°                      CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            n-propyl CH.sub.3                                                                            155-160°                       CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            ##STR22##                                                                              CH.sub.3                                                                            158-160°                     CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            n-butyl  OCH.sub.3                                                                           188-190°                      CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                          Cl    187-189°                      CO.sub.2 CH.sub.3                                                                            H    OC.sub.2 H.sub.5                                                                    Cl       CH.sub.3                                                                            171-173°                      CO.sub.2 C.sub.2 H.sub.5                                                                     H    Cl    CH.sub.3 OCH.sub.3                                   ##STR23##     H    OCH.sub.3                                                                           F        OCH.sub. 3                                 CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               H    CH.sub.3                                                                            Cl       H                                          CO.sub.2 CH.sub.2cyclo-C.sub.3 H.sub.5                                                       H    Br    OCH.sub.3                                                                              OCH.sub.3                                  CO.sub.2 CH.sub.2cyclo-C.sub.6 H.sub.11                                                      H    OCH.sub.3                                                                           CH.sub.3 OCH.sub.3                                  CO.sub.2cyclo-C.sub.6 H.sub.11                                                               H    CH.sub.3                                                                            OCH.sub.3                                                                              CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                         H    CH.sub.3                                                                            Cl       CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 OCH(CH.sub.3).sub.2                                               H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.2 CH(CH.sub.3)On-C.sub.3 H.sub.7                                             H    H     Cl       CH.sub.3                                   CF.sub.3       H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   Cl                                         NO.sub.2       H    OCH.sub.3                                                                           Br       OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   SO.sub.2 CH(CH.sub.3).sub.2                                                                  H    CH.sub.3                                                                            Cl       CH.sub.3                                   SO.sub.2n-C.sub.4 H.sub.9                                                                    H    CH.sub.3                                                                            OCH.sub.3                                                                              CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CH.sub.2 Cl                                                                   Cl    196-201°                      CO.sub.2 CH.sub.3                                                                            H    Cl    CH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                                                           167-171°                      SO.sub.2 N(CH.sub.3).sub.2                                                                   H    H     CH.sub.3 OCH.sub. 3                                  ##STR24##      H    H     Cl       CH.sub.3                                  SO.sub.2 N(n-C.sub.4 H.sub.9).sub.2                                                          H    CH.sub.3                                                                            I        CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            5-Cl H     Cl       H                                          CO.sub.2 C.sub.2 H.sub.5                                                                     5-F  CH.sub.3                                                                            I        CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            5-Br H     OCH.sub.3                                                                              CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            5-NO.sub.2                                                                         H     Cl       H                                          CO.sub.2 CH.sub.3                                                                            5-CH.sub.3                                                                         H     Cl       H                                          CO.sub.2 CH.sub.3                                                                            5-OCH.sub.3                                                                        H     Cl       H                                          CO.sub.2 CH.sub.3                                                                            5-CF.sub.3                                                                         CH.sub.3                                                                            NO.sub.2 CH.sub.3                                    ##STR25##      H    CH.sub.3                                                                            NO       OCH.sub.3                                 CO.sub.2 CH.sub.3                                                                            H    OCH.sub.3                                                                           F        OCH.sub.3                                                                           >300°                         CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H    OCH.sub.3                                                                           F        OCH.sub.3                                                                           >300°                          ##STR26##      H    H     Cl       CH.sub.3                                  CO.sub.2 CH.sub.2 CHClCH.sub.3                                                               H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CN       CH.sub.3                                   CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-Cl OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                  CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 5-NO.sub.2                                                                         OCH.sub.3                                                                           OCH.sub.2 CH.sub.2 OCH.sub.3                                                           OCH.sub.3                                  CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    Br    CH.sub.3 OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                            H    C.sub.2 H.sub.5                                                                     CH.sub.3 CH.sub.3                                   CO.sub.2 CH(CH.sub.3)CHCH.sub.2                                                              H    OCH.sub.3                                                                           OCH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                  CO.sub.2 CH.sub.2 CHBrCH.sub.2 Br                                                            H    OC.sub.2 H.sub.5                                                                    Cl       CH.sub.3                                   SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                            H    OCH.sub.3                                                                           F        OCH.sub.3                                   ##STR27##     5-Br OCH.sub.3                                                                           Cl       OCH.sub.3                                  NO.sub.2       H    CH.sub.3                                                                            CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                      CH.sub.3                                   NO.sub.2       H    CH.sub.3                                                                            NO       CH.sub.3                                   CF.sub.3       H    H     Cl       H                                          SO.sub.2 CH(CH.sub.3).sub.2                                                                  H    OCH.sub.3                                                                           F        OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Cl       CH.sub.3                                   SO.sub.2 C.sub.2 H.sub.5                                                                     5-Cl OCH.sub.3                                                                           F        OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                H    H     Cl       CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                   H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            5-NO.sub.2                                                                         OCH.sub.3                                                                           Cl       OCH.sub.3                                  CO.sub.2 (CH.sub.2).sub.5 CH.sub.3                                                           H    H     F        H                                          CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CH(CH.sub.3).sub.2                                                                           H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   Cl                                         NO.sub.2       H    CH.sub.3                                                                            I        CH.sub.3                                   NO.sub.2       H    OCH.sub.3                                                                           CH.sub.2 CHCH.sub.2                                                                    Cl                                         CO.sub.2 C.sub.2 H.sub.5                                                                     H    CH.sub.3                                                                            Cl       CH.sub.3                                   CO.sub.2 CH.sub.3                                                                            H    H     Cl       H                                          CO.sub.2n-C.sub.4 H.sub.9                                                                    H    CH.sub.3                                                                            Cl       OCH.sub.3                                  CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                H    CH.sub.3                                                                            Br       OCH.sub.3                                  CO.sub.2 CH.sub.2 CF.sub.3                                                                   H    CH.sub.3                                                                            CO.sub.2 CH.sub.3                                                                      CH.sub.3                                   Cl             H    OCH.sub.3                                                                           F        OCH.sub.3                                                                           216-219°                       ##STR28##      H    CH.sub.3                                                                            OCH.sub.2 CH.sub.2 OCH.sub.3                                                           H                                          ##STR29##      H    OCH.sub.3                                                                           CHO       OCH.sub.3                                 ##STR30##      H    OCH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                  ##STR31##      5-Cl                                                                               CH.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                     CH.sub.3                                   ##STR32##      H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                  ##STR33##      5-NO.sub.2                                                                         H     Cl       CH.sub.3                                   ##STR34##      H    Cl    CH.sub.2 CH.sub.2 Cl                                                                   OCH.sub.3                                  ##STR35##      H    Cl    CH.sub.2 CHCH.sub.2                                                                    OCH.sub.3                                  ##STR36##      H    H     Cl       CH.sub.3                                   ##STR37##      5-Br                                                                               Br    (CH.sub.2).sub.2 CH.sub.3                                                              CH.sub.3                                   ##STR38##      5-CF.sub.3                                                                         Cl    OCH.sub.2 OC.sub.2 H.sub.5                                                             OCH.sub.3                                  ##STR39##      H    CH.sub.3                                                                            CH.sub.3                                                                               CH.sub.3                                   ##STR40##      H    OCH.sub.3                                                                           F        OCH.sub.3                                  ##STR41##      5-OCH.sub.3                                                                        Cl    OCH.sub.2 CH.sub.3                                                                     OCH.sub.3                                  ##STR42##      F    OCH.sub.3                                                                           CH.sub.2 CH.sub.2 OCH.sub.3                                                            Cl                                        SCH.sub.3      5-OCH.sub.3                                                                        OCH.sub.3                                                                           CHO      OCH.sub.3                                   SOCH.sub.3     5-NO.sub.2                                                                         CH.sub.3                                                                            ##STR43##                                                                              CH.sub.3                                  CO.sub.2 CH.sub.2 CH(CH.sub.3)OCH.sub.3                                                      H    CH.sub.3                                                                            Br       CH.sub.3                                   CO.sub.2 H     H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   CO.sub.2 H     H    CH.sub.3                                                                            CH.sub.3 OCH.sub.3                                  CO.sub.2 H     H    H     Cl       CH.sub.3                                    ##STR44##      H    CH.sub.3                                                                            CH.sub.3                                                                               CH.sub.3                                  NO.sub.2       6-Cl CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   Cl             6-Cl OCH.sub.3                                                                           F        OCH.sub.3                                  NO.sub.2       6-CH.sub.3                                                                         CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   SOC.sub.2 H.sub.5                                                                            H    CH.sub.3                                                                            CH.sub.3 CH.sub.3                                   SOn-C.sub.3 H.sub.4                                                                          H    CH.sub.3                                                                            Cl       CH.sub.3                                   SOn-C.sub.4 H.sub.9                                                                          H    OCH.sub.3                                                                           Cl       CH.sub.3                                   NO.sub.2       H    CH.sub.3                                                                            Cl       CH.sub.2 OCH.sub.3                         CO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Cl       CH.sub.2 OCH.sub.3                         SO.sub.2 CH.sub.3                                                                            H    CH.sub.3                                                                            Cl       CH.sub.2 OCH.sub.3                         SO.sub.2 N(CH.sub.3).sub.2                                                                   H    CH.sub.3                                                                            Cl       CH.sub.2 OCH.sub.3                         CO.sub.2 CH(CH.sub.3).sub.2                                                                  H    CH.sub.2 OCH.sub.3                                                                  Cl       CH.sub.2 OCH.sub.3                         __________________________________________________________________________

                  TABLE II                                                        ______________________________________                                         ##STR45##                                                                    B      X        Y            Z     m.p. (°C.)                          ______________________________________                                        Cl     H        Cl           H     204-211°                            Cl     CH.sub.3 Br           CH.sub.3                                         Cl     CH.sub.3 Br           OCH.sub.3                                        Br     CH.sub.3 Cl           CH.sub.3                                         Cl     CH.sub.3 CH.sub.3     CH.sub.3                                         Cl     CH.sub.3 Cl           CH.sub.3                                         Br     CH.sub.3 CH.sub.3     CH.sub.3                                         Cl     CH.sub.3 Cl           OCH.sub.3                                        Cl     H        Cl           CH.sub.3                                         Br     H        Br           CH.sub.3                                         Cl     OCH.sub.3                                                                              CH.sub.3     CH.sub.3                                         Cl     Cl       Cl           CH.sub.3                                         Cl     Cl       CH.sub.2 CH.sub.2 Cl                                                                       CH.sub.3                                         Cl     Cl       CH.sub.2 CHCH.sub.2                                                                        Cl                                               Br     Cl       CH.sub.2 CHCH.sub.2                                                                        OCH.sub.3                                        Cl     CH.sub.3 CH.sub.3     C.sub.2 H.sub.5                                  Cl     Cl       Br           Cl                                               Br     CH.sub.3 CH.sub.2 CHCH.sub.2                                                                        Cl                                               Cl     OCH.sub.3                                                                              CH.sub.2 CHCH.sub.2                                                                        Cl                                               Cl     OCH.sub.3                                                                              F            OCH.sub.3                                        Br     CH.sub.3 I            CH.sub.3                                         Cl     CH.sub.3 I            CH.sub.3                                         Cl     CH.sub.3 CN           CH.sub.3                                         Cl     OCH.sub.3                                                                              CH.sub.2 CH.sub.2 Cl                                                                       Cl                                               Cl     CH.sub.3 NO           CH.sub.3                                         ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, suspensions,emulsions, wettable powders, emulsifiable concentrates and the like.Many of them can be applied directly. Sprayable formulations can beextended in suitable media and used at spray volumes of from a fewliters to several hundred liters per hectare. High strength compositionsare used primarily as concentrates which are to be diluted prior toultimate use. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the approximateproportions set forth in Table 2.

                  TABLE 2                                                         ______________________________________                                                   Weight Percent*                                                               Active                                                                        Ingredient                                                                            Diluent(s) Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                           20-90      0-74      1-10                                        Oil Suspensions,                                                               Solutions                                                                     Emulsions                                                                     (including                                                                    Emulsifiable                                                                  Concentrates)                                                                              5-50     40-95      0-15                                        Aqueous Suspensions                                                                        10-50     40-84      1-20                                        Dusts         1-25     70-99      0-5                                         Granules and Pellets                                                                       0.1-95      5-99.9   0-15                                        High Strength                                                                  Compositions                                                                              90-99      0-10      0-2                                         ______________________________________                                         *Active Ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can be present, depending onthe intended use and the physical properties of the compound. Higherratios of surfactant to active ingredient are sometimes desirable, andare achieved by incorporation into the formulation, or by tank mixing.

Some typical solid diluents are described in Watkins, et al., "Handbookof Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, New Jersey, but other solids, either mined or manufactured,may be used. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide", 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as wellas Sisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York, 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending, and usually grinding, as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets can be made byspraying the active material on preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7,line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col.7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167, 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Col. 3, line 66 throughCol. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

Unless indicated otherwise, all parts are by weight in the followingexamples.

EXAMPLE 13 High Strength Concentrate

    ______________________________________                                        Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]-                            aminosulfonyl}benzoate     98.5%                                              silica aerogel             0.5%                                               synthetic amorphous fine silica                                                                          1.0%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce ahigh strength concentrate essentially all passing a U.S.S. No. 50 sieve(0.3 mm openings). This material may then be formulated in a variety ofways known to those skilled in the art.

EXAMPLE 14 Oil Suspension

    ______________________________________                                        Methyl 2-{[(4-chloro-6-methoxy-5-methylpyrimidin-                             2-yl)aminocarbonyl]aminosulfonyl}-                                            benzoate                    25%                                               polyoxyethylene sorbitol                                                      hexaoleate                   5%                                               highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingsuspension may be applied directly, but preferably after being extendedwith oils or emulsified in water.

EXAMPLE 15 Wettable Powder

    ______________________________________                                        Methyl 2-{[(4-chloro-6-methoxy-5-methylpyrimidin-                             2-yl)aminocarbonyl]aminosulfonyl}-                                            benzoate                    40%                                               dioctyl sodium sulfosuccinate                                                                             1.5%                                              sodium ligninsulfonate       3%                                               low viscosity methyl cellulose                                                                            1.5%                                              attapulgite                 54%                                               ______________________________________                                    

The ingredients are thoroughly blended, passed through an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 16 Wettable Powder

    ______________________________________                                        Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]-                            aminosulfonyl}benzoate     80%                                                sodium alkylnaphthalenesulfonate                                                                         2%                                                 sodium ligninsulfonate     2%                                                 synthetic amorphous silica 3%                                                 kaolinite                  13%                                                ______________________________________                                    

The ingredients are blended and coarsely ground in a hammer mill toproduce particles essentially all below 100 microns in size. Thematerial is then reblended, sifted through a U.S.S. No. 50 sieve (0.3 mmopening) and packaged.

EXAMPLE 17 Wettable Powder

    ______________________________________                                        Methyl 2-{[(4-chloro-6-methoxy-5-methylpyrimidin-                             2-yl)aminocarbonyl]aminosulfonyl}-                                            benzoate                  65%                                                 dodecylphenol polyethylene                                                    glycol ether              2%                                                  sodium ligninsulfonate    4%                                                  sodium silicoaluminate    6%                                                  montmorillonite (calcined)                                                                              23%                                                 ______________________________________                                    

The ingredients are thoroughly blended. The liquid surfactant is addedby spraying upon the solid ingredients in the blender. After grinding ina hammer mill to produce particles essentially all below 100 microns,the material is reblended, sifted through a U.S.S. No. 50 sieve (0.3 mmopening) and packaged.

EXAMPLE 18 Wettable Powder

    ______________________________________                                        Methyl 2-{[(5-chloropyrimidin-2-yl)aminocarbonyl]-                            aminosulfonyl}benzoate     50%                                                sodium alkylnaphthalenesulfonate                                                                         2%                                                 low viscosity methyl cellulose                                                                           2%                                                 diatomaceous earth         46%                                                ______________________________________                                    

The ingredients are blended, coarsely hammer milled and then air milledto produce particles of active essentially all below 10 microns indiameter. The product is reblended before packaging.

EXAMPLE 19 Granule

    ______________________________________                                        wettable powder of Example 18                                                                       10%                                                     attapulgite granules  90%                                                     (U.S.S. #20-40; 0.84-0.42 mm)                                                 ______________________________________                                    

A slurry of wettable powder containing 50% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 20 Extruded Pellet

    ______________________________________                                        Methyl 2-{[(4-chloro-6-methoxy-5-methylpyrimidin-                             2-yl)aminocarbonyl]aminosulfonyl}-                                            benzoate                    25%                                               anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

Utility

The compounds of the present invention are effective herbicides. Theyhave utility for broad-spectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful forselective pre- or post-emergence weed control in crops such as wheat andbarley. Certain of the subject compounds control nutsedge (Cyperus spp.)and some compounds may be used for selective weed control in soybeans.The compounds of this invention also possess plant growth regulantactivity.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crops species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.125 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for selective weed control orfor situations where only short-term persistence is required.

Combinations of the compounds of Formula I with known herbicides provideeffective control of weeds in small grain crops such as wheat andbarley. Typical herbicides that may be used arechlorotoluron[3-(3-chloro-4-methylphenyl)-1,1-dimethylurea], MCPP[(±)-2-(4-chloro-2-methylphenoxy)propanoic acid], metoxuron[3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea], methabenzthiazuron[1-(benzothiazol-2-yl)-1,3-dimethylurea], dichlofop[(methyl-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate)],tri-allate[S-2,3-dichloroallyl di-isopropylthiocarbamate],isoproturon-[3-(4-isopropylphenyl)-1,1-dimethylurea], ordifenzoquat[1,2-dimethyl-3,5-diphenylpyrazolium ion].

The compounds of Formula I may also be combined with other herbicidesand are particularly useful in combination with ureas, such as3-(3,4-dichlorophenyl)-1,1-dimethylurea,3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea and1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl) urea; the triazines such as2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine; the uracils suchas 5-bromo-3-sec-butyl-6-methyluracil; N-(phosphonomethyl)glycine;3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione;N,N-dimethyl-2,2-diphenylacetamide; 2,4-dichlorophenoxyacetic acid (andclosely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate;diisopropylthiolcarbamic acid, S-(2,3,3-trichloroallyl)ester;ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate;4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one;3-isopropyl-1H-2,1,3-benzothiodiazin-(4)-3H-one-2,2-dioxide;α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine;1,1'-dimethyl-4,4'-bipyridinium ion; monosodium methanearsonate; and2-chloro-2',6'-diethyl(methoxymethyl)acetanilide.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Results from the tests are expressed in terms of plant response ratingswhich are composed of a number and a letter. The number describes theextent of the response and ranges from zero to ten with zerorepresenting no response and ten representing 100% response. The letterdescribes the type of the response, as explained below.

A=growth acceleration

U=unusual pigmentation

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

The ratings "6Y" and "6F" are exceptions to the above described ratingsystem, and represent abscised buds or flowers and delayed flowering,respectively.

Test Procedure A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory(Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice,wheat and nutsedge tubers (Cyperus rotundus) were planted in a growthmedium and treated pre-emergence with a non-phytotoxic solvent solutionof the compounds of Table A. At the same time, cotton having five leaves(including cotyledonary ones), bush beans with the third trifoliate leafexpanding, crabgrass with two leaves, barnyardgrass with two leaves,wild oats with two leaves, cassia with three leaves (includingcotyledonary ones), morningglory with four leaves (includingcotyledonary ones), cocklebur with four leaves (including thecotyledonary ones), sorghum with four leaves, corn with four leaves,soybean with two cotyledonary leaves, rice with three leaves, wheat withone leaf, and nutsedge with three to five leaves were sprayed with anonphytotoxic solvent solution of the compounds of Table A. Othercontainers of the above mentioned weeds and crops were treated pre- orpost-emergence with the same nonphytotoxic solvent so as to provide asolvent control. A set of untreated control plants was also included forcomparison. Pre-emergence and post-emergence treated plants and controlswere maintained in a greenhouse for sixteen days, then all treatedplants were compared with their respective controls and rated visuallyfor response to treatment. The data in Table A shows that the compoundsof this invention are very effective as herbicides and often are capableof modifying plant growth.

    TABLE A      POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR46##      0.4 9C 2C,8G 2C,9G 5G 2C,5G 5G 4G 2C,7H 0 0 1C,3H 4C,9G 3C,8G 8H      ##STR47##      0.42 3C,7G,6Y6D,9G,6Y 5C,9G4C,9G 5C,9G5C,9G 5C,9G9C 2C,9H1C,9H 8G9G     5G1C,8H 8H9H 03G 1C,3G2C,7G 2C,6H2C,9H 2C,8G5H,8G 9G2C,9G 2H,9G9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR48##      0.4 6G 6G 8G 9G 0 2C,9H 2G 2G 1C,8G 2H 9H 9H      ##STR49##      0.42 --9G 9G9G 5C,9G3C,9G 10E10E 3G6G 8H9H 8G9H 2C,9G9H 1C,9G2C,9G      2     1C,3GC,8H 10E10E 9G9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR50##      2 1C,5G 1H 2G 2G 3G 2G 1C,3G 5C,9H 1C 1C 5C,6H 3G 9C 5C,9G      ##STR51##      2 3C,4H,6Y 1C 5C 9C 7G 1C,8G 2C,5G 1C,4H 0 0 2C,6H 2C -- 1C,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR52##      2 3G 10E 3G 5G 2C,5G 2C,7G 1C 1C 2C,5G 2H 9H 9H      ##STR53##      2 9G 9H 9G 10E 3G 2C,6G 1C,3G 2C 2C,8G 1C,1H 10E 3C,9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR54##      2 9D,9G,6Y 2H,4C,9G 5C,9G 3C,9H 3C,9G 4C,9G 0 3C,8H 1C 1C 5C,9G 9C 9C     2C,8G      ##STR55##      2 7D,9G,6Y 7C,9G 7C,9G 9C 9C 9C 2C,5G 9C 3C,6H 3C,5H 7U,9G 5C,9G --     3U,5C,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR56##      2 9G 9G 2C,9G 10E 1C,5G 9H 7G 1G 9G 9H 10E 2C,7G      ##STR57##      2 9G 9H 9G 10E 3C,9G 10H 9H 9H 10E 9H 10E 2C,9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR58##      2 0 0 0 0 0 0 1C 2C 0 0 8C 0 1C 2C      ##STR59##      20.4 6D,9G,6Y3C,7G,6Y 4C,9G5C,9G 5C,9G5C,9G 9C5C,9G 1C,9H2C,9H 9G8G     1C,8H5G 9H8H 3G0 2C,7G1C,3G 2C,9H2C,6H 5H,8G2C,8G 2C,9G9G 9G2H,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR60##      2 0 0 0 10E 0 0 0 0 0 0 0 0      ##STR61##      20.4 9G-- 9G9G 3C,9G5C,9G 10E10E 6G3G 9H8H 9H8G 9H2C,9G 2C,9G1C,9G      1     2C,8HC,3G 10E10E 9H9G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR62##      0.4 9C 2C,8G 2C,9G 5G 2C,5G 5G 4G 2C,7H 0 0 1C,3H 4C,9G 3C,8G 8H      ##STR63##      0.4 9C 3C,8G 1C 9C 2C,5H 5C,8G 0 2C,5H 0 0 8H 2C,9G 1C,9G 2H,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR64##      0.4 6G 6G 8G 9G 0 2C,9H 2G 2G 1C,8G 2H 9H 9H      ##STR65##      0.4 4G 2C,9G 2C,9G 9G 0 2C,8H 2G 0 9H 5G -- 2C,9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR66##      0.4 9C 3C,9G 9C 9C 2C,7G 9C 2C,7G 9C 9C 2C,9G 8U,9G 5C,9G 9C 9C      ##STR67##      0.4 7C,9G,6Y 3U,5C,9G 2C,8G 5C,9G 6C,9G 10C 2C,7H 5C,9H 9G 1C,8G 1C,9G     5C,8G -- 5U,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR68##      0.4 9G 9G 9G 10E 2G 9H 9G 9G 10E 9H -- 8C,9H      ##STR69##      0.4 9G 9G 9G 10E 2G 2C,9H 9G 9G 9G 9H 10E 10H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-Crab-      yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia sedge     grass grass OatsWheat Corn bean Rice ghum      ##STR70##      0.4 7C,9G 9C 9C 9C 9C 8C,9G 6C,9G 9C 9C 2C,5G 8U,9G 6C,9G 3C,9G 9C      ##STR71##      0.4 9C 3C,4H,9G 3C,9G 4C,9G 3C,7G 2C,9G 3G 9H 2G 0 2C,8H 3H,9G 1C,8G     2C,9H       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR72##      0.4 9G 9G 8G 10E 9H 9H 9H 9H 9H 9H 10E 1C,9H      ##STR73##      0.4 9G 9H 9G 9G 0 3C,9H 2C,8G 2G 2C,8H 1C,2H 9H 1C,8G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR74##      0.4 9C 6C,9G 9C 5C,9G 3C,4H 1C,9G 3G 3C,9H 2G 0 2C,9H 4C,9G 9C 1C,9G      ##STR75##      0.4 9C 3C,4H,9G 10C 5C,9G 2C,6G 1C,7G 3G 1C,5H 0 0 1C,4H 3H,9G 1C,2G     2C,9H       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy- Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR76##      0.4 9G 9H 9G 10E 1C 3C,9H 1C,5G 5G 9G 6H 9H 9H      ##STR77##      0.4 6G 9H 2C,6G 1C,8G 2G 2G 0 0 1C,7H 2G 7H 2C,5H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR78##      0.4 10D,9G 3C,7G 3C,7G 3C,8G 1C 2G 3G 3H 0 0 2C,8H 3C,7G 2C,6G 1C,5G      ##STR79##      0.4 9D,9G,6Y 9C 9C 9C 9C 9G 1C,8G 4C,9G 1C,7G 4C,8G 1U,9G 5C,9G 1C,7G     9G  PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR80##      0.4 6G 8G 5G 3G 2G 4C 4G 4G 1C 2H 3G 2C      ##STR81##      0.4 8G 9H 8G 10E 2C,8G 9H 1C,7G 1C,8G 1U,9G 5H 10E 1U,9G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR82##      0.4 6C,9G,6Y 2C,3H,9G 2C,9G 2C,2H,7G 6D,7G 9G 1C,6G 2C,9G 6G 2C,6G     1U,8G 1C,4G 1C,7G 9G      ##STR83##      0.4 9C 2C,3H,6G 9C 9C 1C,5G 9G 1C,5G 2C,9H 0 0 1C,9H 9C 2C,9G 1C,7G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR84##      0.4 6G 8G 2C 1C,7G 2G 2C,6G 2G 2G 1C,7G 2A 2C,9H 1C,8G      ##STR85##      0.4 9G 9H 8H 10E 0 1C,5G 6G 4G 1C,6G 5H 8H 0       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR86##      0.4 9C 5C,9G 2C,8G 9C 2C,5G 1C,7G 5G 3C,9H 0 0 10C 9C 3C,9G 1C,9H      ##STR87##      0.4 3C,9D,9G 3C,3H,9G 4C,9G 3C,9H 2C,4G 2C,8G 3C 3C,9H 0 0 2C,8H 2C,9G     5C,9G 2C,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR88##      0.4 9G 9H 8G 10E 1G 9H 6G 6G 9H 9H 10E 9H      ##STR89##      0.4 9G 9H 3C,9G 2C,9G 2G 3C,9H 1C,7G 5G 9G 9H 10E 5C,9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR90##      0.4 9C 6C,9G 3C,9G 3C,9G 5C,9G 1C,6G 1C 1C,6H 0 0 1C,4G 10C 7G 1C,8G      ##STR91##      0.4 8D,9G,6Y 4C,8D,9G 5C,9G 6C,9G 6C,9G 5C,8G -- 3C,7H 0 0 1C 9C --     2U,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR92##      0.4 9G 9G 8G 10E 4G 2C,9H 1C 0 1C,6G 9H 10E 1C,8G      ##STR93##      0.4 9G 8H 9G 10E 1C,5G 3C,9H 3G 0 7G 9H 10E 9H       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR94##      0.4 8D,9G,6Y 2C,3H,9G 10C 5C,9G 2C,2G 0 0 2G 0 0 1C,3G 1C,3H 2G 2G      ##STR95##      0.4 10D,9G,6Y 2C,3H,9G 10C 3C,9G 2C,3G 1C,3G 1C 1C 0 0 1C,3G 2C,8H     1C,4G 7G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR96##      0.4 5G 8H 1C 10E 0 0 0 0 1C,3G 3H 1C,5G 1C      ##STR97##      0.4 8G 8H 7G 4G 0 2C 0 0 1C,3G 6H 3C 0       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR98##      0.4 5C,7G 2C 1C,5G 1C 1C 1C 1C,4G 2C 0 0 1C,4H 1C,5H -- 1C,8G      ##STR99##      0.4 3C,3H,6Y 2C,2H 1C 2C 1C 0 0 0 0 0 1C 1C -- 1C,3H       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR100##      0.4 8G 5H 1C 7G 2G 1C,3G 2G 2G 2C,6G 0 9H 1C,5G      ##STR101##      0.4 5G 6H 2C 2G 5G 3C 0 0 2C,4G 1H 2C,5G 2C,7G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR102##      0.4 2C,2H,6Y 2C,2H 1C,4G,6F 1C,1H 0 0 2G 1G 0 0 0 1C,3G -- 1C,4G      ##STR103##      0.4 6C,7G,6Y 3C,3H,9G 5C,9G 3C,9H 3C,8H 2C 1C,2G 3C,9H 2C,4G 2C,4G     5U,9G 5U,9G 1C,8G 1U,9G       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR104##      0.4 8G 8H 1C,3G 5G 2G 2C 0 0 1C 0 0 3G      ##STR105##      0.4 1C,5G 2C,8G 1C 1C 2G 1C,5G 6G 7G 1C,9G 2C,4G -- 2C,5G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR106##      0.4 8D,9G,6Y 2C,2H,8G 2C,9G 2H,9G 2C,5G 0 0 1C 0 0 1C 2C,9G -- 2C,8H      ##STR107##      0.4 1C 2C,5G 2C 2C 1C 0 0 2G 0 0 0 1C,4G 7G 0       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR108##      0.4 5G 8G 1C 0 0 0 0 2G 1C, 4G 0 3G 3G      ##STR109##      0.4 8G 9G 6G 0 0 1C 0 0 2C, 4G 0 -- 1C,3G       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR110##      0.4 2C,1H 2C,5G 3C,8G 1C,5G 1C 0 1C 1C 0 0 0 2C -- 0      ##STR111##      0.4 3C,8G,6Y 2C,3H,9G 0 3G 2C,7G,5X 0 0 0 0 0 2H 1C 0 0       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR112##      0.4 3G 5G 0 0 3G 0 0 0 1C,6G 1H 0 0      ##STR113##      0.4 0 0 0 0 0 0 0 0 10E 0 0 0       POST-EMERGENCE     Morn-     Barn-         Bush-  ing- Cock-  Nut-     Crab- yard- Wild   Soy-  Sor-  kg/ha bean Cotton glory lebur Cassia     sedge grass grass Oats Wheat Corn bean Rice ghum      ##STR114##      0.4 4C,9G,6Y 4C,9G 4C,9H 2C,9G 1C,4G 1C,9G 2H 2C,9H 0 0 2G 9C 1C,9G     1C,9H       PRE-EMERGENCE   Morn-     Barn-         ing- Cock-  Nut- Crab- yard-     Wild   Soy-  Sor-  kg/ha glory lebur Cassia sedge grass grass Oats Wheat     Corn bean Rice ghum      ##STR115##      0.4 9G 9G 8G 9G 1C 2C,9H 1C,5G 1C,8G 2C,7G 2C,8H 10E 2C,8H

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatus), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus),morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sidaspinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugarbeets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B. Certain compounds from within the scope of the inventionhave utility for selective weed control in soybeans.

    TABLE B      PRE-EMERGENCE ON FALLSINGTON SILT LOAM          Barn-            Rate Crab- yard-  Wild Johnson- Dallis- Giant Ky.     Cheat- Sugar-  kg/ha grass grass Sorghum Oats grass grass foxtail     Bluegrass grass beets Corn Mustard      ##STR116##      1/161/4 02G 03G 2H5G,3H 00 00 00 00 00 00 5C,5G6C,6G 00 5C,7G7C,8G      ##STR117##      .062.250 05G 9G,8C9G,9C 9G,8C10C 4G7G,4C 7G,5H10C 6G9G,8C 9G10C     7G,6C8G,8C 10C10E 6G,5H9C 6G,5H10C 7G8G,3C      ##STR118##      .031.125 6G8G,7C 8G,4C9G,9C 10C10E 7G,2C7G,7C 8G,8C9G,9C 9G,9C10C 8G10C 8     G,7C8G,8C 10C10C 6G7G,5C 10C10C 8G,2C9G,8C      ##STR119##      .062.250 00 06G,3H 3G7G,5H 05G 00 00 03G 4G6G,2C 6G,2C7G,5C 4G6G 00     7G,2C8G,3C      ##STR120##      .062.250 6G7G 8G,8C9G,9C 10C8G,9C 6G,3C6G,3C 8G,5H8G,8C 8G,5C9G,9C      8     7G,4CG,4C 6G,5C6G,5C 8G,7C10C 7G,6C7G,4C 8G,5H8G,9C 8G,8C9G,9C      ##STR121##      .062.250 02G 3G7G,5C 7G,5H10E 02G 3G,3H6G,5H 5G4G 4G3G,2C 5G,3C6G,4C     5G,3H7G,5H 5G,3H6G,3H 06G,3H 6G5G,2C      ##STR122##      0.060.25 00 00 00 00 0 0 00 00 00 06G,3H 4G8G,7C 00 6G3C,8G      ##STR123##      .031.062.125.250.5.51 04G3G10C7G,4C7G,2C7G,5C 2G3G,2C6G,4C7G,5H8G,7C7G,8     C9G,8C 8G,5H3G10C9G,9C10C10C9G,9C 2G,2C4G5G,2H7G,7C7G,5C5G,4C6G,4C     5G,3H8G,3C7G,3H10C10E8G,7C10E 7G7G10E10C10E8G,8C10E 3G6G,7C5G,5H9G,9C8G,5     H8G,4C8G,5H  6G,8C10C5G,6C10C8G,9C10C10C 7G,8C6G,8C10E10C10E10C10E     5G5G,6C7G,3C10C8G,8C7G,7C8G,7C 02G7G,5H10C10C7G,8C7G,8C 7G,3C8G,6C6G,3C10     C9G,9C9G,9C9G,9C      ##STR124##      .062.250 00 3G,2C4G,2C 3G5G,2H 00 04G 03G 04G 3G4G 2G6G 6G7G 05G,3H     6G7G,6C      ##STR125##      .062.250 03G 07G,2H 4G9G,9C 02G 3G7G,3H 06G 05G,5C 5G8G,8C 8G,9C8G,5C     05G,2C 00 7G,5C9G,9C      ##STR126##      .125.5 00 4G6G,3C 6G,3H7G,3H 00 3G5G 05G 3G6G,2C 05G 05G,3C 5G,3C7G,7C  4     0G 7G,2C8G,3C      ##STR127##      .125.5 04G 5G8G,5H 8G,5H9G,8C 00 6G,3H7G,3H 05G 3G10C 4G6G 5G,3C6G,5C     6G,5C7G,7C 05G 8G9G,8C      ##STR128##      0.060.25 02G 03G 2H5G,3H 00 00 00 00 00 00 5G,5C6G,6C 00 7G,5C8G,7C      ##STR129##      0.0150.030.12 3G3G,2C6G,2C 5G,3C7G,4C8G,5H 10C10C10E 4G5G7G,3H 7G,3H8G,5     H8G,5C 4G3G,2C6G 5G8G,9E10C 5G7G,4C8G,8C 6G,3C7G,6C10C 6G,3C6G,3C8G,7C     6G,3H7G,5H8G,5H 9G,9C8G,8C9G,9C        Rate Cockle-    Morning-   Velvet- Jimson-  kg/ha bur Pigweed     Nutsedge Cotton glory Cassia Teaweed leaf weed Soybean Rice Wheat      ##STR130##      1/161/4  --7G 5G10E 3G8G 4G,3H8G 5G,3H7G,5C 05G,7C 03G 05G,4H 02G 02C     03G,3C 00      ##STR131##      .062.250 6G6G,2H ---- 8G10E 6G6G,2H 07G 5G7G ---- 05G,3H 3G,3C5G,2C     5G,5H5G,3H 10E10E 4G6G      ##STR132##      .031.125 5G7G,5H ---- 10E10E 6G8G 5G7G 4G6G 7G7G 5G,3H9G,9C 3H5G,5C     7G,5H8G 10E10E 6G8G,6C      ##STR133##      .062.250 5G4G ---- 07G 3G6G,5H 06G 3G7G 05G 05G,3H 00 00 3G7G,3C 03G,3C      ##STR134##      .062.250 7G8G,9C ---- 10E10E 8G8G,3C 7G,3C8G,4C 7G,5C7G,7C 8G,4C9G,7C     8G,8C10C 4G4G 5G,6C7G,7C 10E10E 6G,3C6G,4C      ##STR135##      .062.250 3G-- ---- 10E10E 06G 2G6G 4G8G,8C 00 2G5G,3H 00 2G 6G,4H     7G,5H10E 3G5G      ##STR136##      0.060.25 06G ---- 4G9G 00 04G 02G 00 05G,3H 00 02H 06G,3H 00      ##STR137##      .031.062.125.250.5.51 3G5G6G7G,5H 6G6G,3H6G -------------- 07G8G9G10E10E1     0E 5G2G4G7G7G7G8G 02G07G7G,2C6G7G 006G,3C8G,7C8G,6C6G9G,9C 0--5G--5G,3C3G1     0E 005G10C6G,5H5G,3C6G,5H 03G3G8G,8C5G3G5G 002G06G5G,3H5G,3H 8G,8C7G,8C10     E10E10E10C10E 5G,3C6G,3C5G7G,5C8G,5H8G,7C5G,3C      ##STR138##      .062.250 3G4G ---- 10E10E 03G 04G 06G 04G 4G6G,3H 00 04G,3H 7G,5E9G,9C  2     0G      ##STR139##      .062.250 02G ---- 06G 00 03G 00 ---- 05G 00 05G,5H 5G7G,4C 02G      ##STR140##      .125.5 5G6G,2C ---- 10E10E 5G7G 06G,3H 3G6G 6G,2C8G,8C 5H6G,8C 03G      7     6G,3HG,7H 6G,6C10C 02G      ##STR141##      .125.5 6G,3H6G,5C ---- 10E10E 7G8G 4G6G 7G8G,8C 6G,5C9G,9C 5H9G,9C 04G     8G,8H8G,8C 10C10E 03G      ##STR142##      0.060.25 --7G 5G10E 3G8G 4G,3H8G 5G,3H7G,5C 05G,7C 03G 05G,4H 02G 02C     03G,3C 00      ##STR143##      0.0150.030.12 6G,3H6G8G,5H ------ 10E10E10E 6G4G8G 8G8G8G,5C 7G6G8G,8C     8G,8C8G,8C9G,8C 8G,8C5G,5H 10C 5G,5C7G,5C6G,5C 8G,8H8G,5H8G,9C 10C10E10E 4     G3G6G

Test C

Twenty-five cm diameter plastic pots filled with Fallsington silt loamwere planted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum,velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Cassia(Cassia tora), morningglory (Ipomoea hederacea), jimsonweed (Daturastramonium), cocklebur (Xanthium pennsylvanicum), crabgrass (Digitariaspp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloacrusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua).Approximately 21/2 weeks after planting, the young plants and the soilaround them were sprayed overall with the test chemicals dissolved in anonphytotoxic solvent. Fourteen days after treatment, all species werecompared to untreated controls and visually rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

                                      TABLE C                                     __________________________________________________________________________    OVER-THE-TOP SOIL/FOLIAGE TREATMENT                                           __________________________________________________________________________                                                   Morn-   Jim-                                          Rate                                                                              Soy-                                                                              Vel-                                                                              Ses-        ing-    son-                                                                              Cock-                                     kg/ha                                                                             beans                                                                             vetleaf                                                                           bania                                                                             Cassia                                                                            Cotton                                                                            glory                                                                             Alfalfa                                                                           weed                                                                              lebur              __________________________________________________________________________     ##STR144##            1/16 1/4                                                                          4C,8G 8C,10G                                                                      6C,10G 10C                                                                        5C,8G 9C,10G                                                                      5C,8G 3C,10G                                                                      3C,9G 3C,10G                                                                      6C,10G 10C                                                                        6C,10G 6C,10G                                                                     5C,10G 5C,10G                                                                     5C,10G 5C,10G       ##STR145##            1/4 1/16                                                                          10G,8C 10G,7C                                                                     -- --                                                                             -- --                                                                             10C 10C                                                                           10G,4C 9G,7C                                                                      9G,7C 4G                                                                          8C 8C                                                                             -- --                                                                             10G,8C 7G,3C        ##STR146##            1/8 1/32                                                                          10G,7C 10G,6C                                                                     10C 9G,1C                                                                         9C 10G,7C                                                                         9G,5C 8G,4C                                                                       6G,2C 5C,1C                                                                       7G,5H 10G,7C                                                                      9C 8G,3C                                                                          10C 5G,2C                                                                         8G,4C 3G            ##STR147##            1/4 1                                                                             10G,7C 8C                                                                          10G,7C 10G,6C                                                                    10G,6C 10G,8C                                                                     9G,4C 10G,5C                                                                      5G,2C 7G,2C                                                                       10G,6C 10G,8C                                                                     3G,2C 8C                                                                          -- --                                                                             5G,7H 9G,4C         ##STR148##            1/4 1/16                                                                          5G,2C 2G                                                                          10G,2C 7G                                                                         8G,2C 3G                                                                          4G,1C 1G,2C                                                                       4G,2C 3G,1C                                                                       10G,4C 8G                                                                         2 0 1C,3G 0                                                                           3G,1C 2G            ##STR149##            1/16 1/64                                                                         10C 7G,4C                                                                         7G,3C 1C                                                                          8G,3C 0                                                                           7G,3C 3G,1C                                                                       7G,3C  2G                                                                         10G,4C --                                                                         6C 1C                                                                             2G,2C 0                                                                           3G,1C 0             ##STR150##            1/2 1/4                                                                           10G,7C 10G,7C                                                                     10C --                                                                            -- --                                                                             10G,7C 10G,6C                                                                     8G,3C 8G,4C                                                                       10G,7C 4G                                                                         9C 8C                                                                             -- --                                                                             3G,2C 0            __________________________________________________________________________                                               Barn-                                                     Rate    Crab-   Nut-                                                                              yard-   Giant                                                                             Wild                                                                              Sorg-                                     kg/ha                                                                             Corn                                                                              grass                                                                             Rice                                                                              sedge                                                                             grass                                                                             Wheat                                                                             Foxtail                                                                           Oats                                                                              hum                __________________________________________________________________________     ##STR151##            1/16 1/4                                                                          5H,8G 3H,9G                                                                       3G 3G                                                                             4C,10G 3C,10G                                                                     0 0 3C,10G 4C,10G                                                                     6G 10G                                                                            0 0 3G 7G                                                                             8G,2H 10G,2H        ##STR152##            1/4 1/16                                                                          9G,5U 9G,7H                                                                       7G 3G                                                                             9G,4C 7G,1C                                                                       4G 8G,2C                                                                          10G,5C 9G                                                                         4G 2G                                                                             -- --                                                                             10G,7C 5G,2C                                                                      10C 8G,3C           ##STR153##            1/8 1/32                                                                          5G,2C 7G,5H                                                                       2G  7G,6C                                                                         10C 8G,5C                                                                         8G,3C 7G                                                                          9G,6C 5G,2C                                                                       7G 2G                                                                             5G 0                                                                              7G 2G                                                                             9G,3C 7G,1C         ##STR154##            1/4 1                                                                             5G,7H 4G,4H                                                                       0 1G                                                                              4G,1C 4G,1C                                                                       10G,6C 8G,5C                                                                      5G,2C 6G,3C                                                                       0 0 6G 6G                                                                             0 0 6G 8G               ##STR155##            1/4 1/16                                                                          3G,1C 0                                                                           2G,2C 0                                                                           -- --                                                                             3G 0                                                                              5G,1C 0                                                                           0  1G                                                                             3G 2G                                                                             0 0 9G,3C 0             ##STR156##            1/16 1/64                                                                         8G,2H 0                                                                           0 0 2G 0                                                                              5G 2G                                                                             2G,1C 0                                                                           0 0 -- --                                                                             0 0 8G,3C 2G,1C         ##STR157##            1/2 1/4                                                                           4G 4G                                                                             -- 5G                                                                             3G 0                                                                              5G 1G                                                                             1C,6G 3G                                                                          0 0 -- --                                                                             3G  3G                                                                            5G,2C 5G,2C        __________________________________________________________________________

Test D

Purple nutsedge (Cyperus rotundus) tubers were planted about 2 cm deepin Fallsington silt loam soil contained in 10 cm diameter plastic pots.Five tubers were planted in each pot. Compounds of this invention weredissolved in an nonphytotoxic diluent and sprayed at 560 l/ha in fourmethods of application: soil surface, tuber/soil, soil incorporated, andpost-emergence. The soil surface spray consisted of spraying thecompound on the surface of the firmed covering soil. The tuber/soilspray consisted of spraying the compound on exposed tubers andsubtending soil before adding the untreated covering soil. Soilincorporated treatment consisted in mixing the compound with thecovering soil before using it to cover the tubers. The post-emergencetreatment was sprayed on nutsedge foliage and the surrounding soilsurface when nutsedge had emerged and grown to a height of about 12 cm.Pots receiving the post-emergence treatments were placed directly in thegreenhouse. Pots receiving the other treatments were misted with about0.3 cm water before being transferred to the greenhouse. Responseratings assessed after four weeks are recorded in Table D based on thesame rating system as described in procedure A.

                  TABLE D                                                         ______________________________________                                         ##STR158##                                                                   Plant Response 4 Weeks after Treatment                                               Pre       Pre          Pre     Post                                    Rate   Surface   tuber + soil soil inc.                                                                             foliar                                  kg/ha  spray     spray        2.5 cm  spray                                   ______________________________________                                        1/64   0         3G           3G      0                                       1/16   2G        8G           7G      0                                       1/4    8G        9E,9G        6E,8G   2C,4G                                   ______________________________________                                    

Test E

Two ten-inch in diameter plastic pans lined with polyethylene linerswere filled with prepared Fallsington silt loam silt. One pan wasplanted with seeds of wheat (Triticum aestivum), barley (Hordeumvulgare), wild oats (Avena fatua), downy brome (Bromus tectorum),cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides),annual bluegrass (Poa annua), green foxtail (Setaria viridis),quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) andripgut brome (Bromus rigidus). The other pan was planted with seeds ofRussian thistle (Salsola Kali), tansy mustard (Descurainia pinnata),smartweed (Polygonum pennsylvanicum), jimhill mustard (Sisymbriumaltissimum), Kochia (Kochia scoparia), shepherd's purse (Capsellabursa-pastoris), false chamomile (Matricaria inodora), black nightshade(Solanum nigrum), yellow rocket (Barbarea vulgaris), wild mustard(Brassica kaber) and wild buckwheat (Polygonum convolvulus). The abovetwo pans were treated pre-emergence. At the same time, two pans in whichthe above plant species were growing were treated post-emergence. Plantheight at the time of treatment ranged from 1-15 cm depending on plantspecies.

The compounds applied were diluted with a nonphytotoxic solvent andsprayed over-the-top of the pans. An untreated control and asolvent-alone were included for comparison. All treatments weremaintained in the greenhouse for 20 days at which time the treatmentswere compared to the controls and the effects visually rated utilizingthe rating system described previously for Test A. The recorded data arepresented in Table E. It may be seen that several of the test compoundsprovide control of a range of weed species without causing injury towheat or barley.

    TABLE E      Pre-emergence         annual   Italian   Rate   wild downy cheat-     black- blue- green quack- rye- ripgut  kg/ha wheat barley oats brome     grass grass grass foxtail grass grass brome      ##STR159##      1/41 00 02G 01G 7G7G 6G7G 6G7G 7G2C,8G 1G2C,4G 5G7G 5G3C,7G 1G2G      ##STR160##      1/641/16 00 00 00 02G 2G3G 00 2G3G 00 00 00 00      ##STR161##      1/641/16 00 00 00 00 03C,4G 02C,3G 1G2C,2G 00 02G 00 00      ##STR162##      1/641/16 00 00 00 00 02G ---- 01G 00 00 00 00      ##STR163##      1/641/16 00 00 00 02G 2G1C,3G ---- 01G 01C 00 02G 00      ##STR164##      1/641/16 00 01G 00 1G2G 2G5G ---- 2C,3G2C,5G 00 03G 2G3G 02G              shep- false black   wild  Rate Russian tansy smart- jimhill     herd's chamo- night- yellow wild buck-  kg/ha thistle mustard weed     mustard Kochia purse mile shade rocket mustard wheat      ##STR165##      1/41 3C,2G4C,5G 9C,9G9C,9G 9C,9G9C,9G8C,9G8C,9G ---- 9C,9G10C 7C,8G7C,9G      2C,7G3C,8G 7C,8G7C,9G 7C,8G 7C,9G 2C,4G3C,7G      ##STR166##      1/641/16 00 2G2C,5G 1G3G 3G5C,7G 05G 3G7C,8G 02C,4G ---- 5G5C,7G 05C,4G 0    1     C,2G      ##STR167##      1/641/16 02C,3G 2G10C ---- 5C,6G6C,7G 4G3C,5G 5C,7G5C,8G 1G4C,3G ----     2G5C,7G 1G7C,7G 00      ##STR168##      1/641/16 01G 2C,3G7C,8G ---- 4G7G 03G 5G8C,9G 1C,2G7C,8G ---- 2G3C,7G   7     4GG 00      ##STR169##      1/641/16 01C,2G 2C,3G9C ---- 8C9C 3G1C,5G 9C10C 7C,8G8C,9G -- --     7C,7G8C,9G 2C,7G3C,7G 01G      ##STR170##      1/641/16 02C,3G 8C10C ---- 9C10C 02G 3C,7G7C,8G 1C,2G6C,7G ---- 7G7C,8G 2     G5C,6G 02C,6G       Post-emergence         annual   Italian   Rate   wild downy cheat-     black- blue- green quack- rye- ripgut  kg/ha wheat barley oats brome     grass grass grass foxtail grass grass brome      ##STR171##      1/41 00 2G3G 2C,2G2C,3G 2C,5G3C,4G 1C,3G2C,6G 1C,3G2C,5G 1C,3G2C,5G     3C,3G4C,5G 3G5G 3G3C,7G 02G      ##STR172##      1/641/16 00 00 00 00 00 00 00 00 00 00 00      ##STR173##      1/641/16 00 02C,4G 00 02G 02C,3G 02C 02C,2G 09C 00 00 01G      ##STR174##      1/641/16 00 00 00 00 1G2G 01G 01G 2G1C,3G 3G4C,5G 03G 00      ##STR175##      1/641/16 00 01C,1G 02C 01C,3G 1G1C,4G 1C,2G1C,3G 00 1C,2G0 3C,4G2C,3G     5C,4G1G 00      ##STR176##      1/641/16 00 2G4C,7G 00 00 02G 1C,1G2C,3G 01C,2G 1G1C,3G 1G2G 2G2C,5G     02G         shep- false black   wild  Rate Russian tansy smart- jimhill     herd's chamo- night- yellow wild buck-  kg/ha thistle mustard weed     mustard Kochia purse mile shade rocket mustard wheat      ##STR177##      1/41 9C,7G10C 10C10C 10C10C 10C10C 10C10C 10C10C 9C,9G10C 2C,4G5C,7G    1     10C0C 10C10C 5C,4G5C,5G      ##STR178##      1/641/16 02C,2G 10C10C 1C5C,5G  10C10C 4G10C 2C,3G3C,5G 2C,2G5C,5G ---- 1     0C10C 10C10C 00      ##STR179##      1/641/16 2C7C 2C,3G9C 2C,2G8C 7C9C 3C,5G5C,5G 2G3C,5G 2C,2G2C ----     01C,2G 2C,3G6C,5G 02C      ##STR180##      1/641/16 10C0 5C,5G0 8C0 7C0 7C1C 10C0 5C,3G1C ---- 2C0 7C,6G0 1C0      ##STR181##      1/641/16 9C10C 1C,2G4C,5G 7C8C 5C,6G7C,7G 6C,7G8C 4C,3G5C,7G 5C,3G7C,5G     ---- 7C7C,7G 2C,5G6C,5G 1C2C,3G      ##STR182##      1/641/16 03C,5G 03C ---- 06C,5G 00 3C3C,5G 04C,5G ---- 03C 1C5C,4G     02C,3G

What is claimed is:
 1. A compound selected from: ##STR183## wherein A is##STR184## B is Cl or Br; X and Z are independently H, CH₃, Br, Cl,OCH₃, CH₂ CH₃, CH₂ OCH₃ or OCH₂ CH₃ ; andY is F, Cl, Br, I, CH₃, CH₂CH₃, CH₂ CH₂ CH₃, (CH₂)₃ CH₃, CH₂ -CH═CH₂, OCH₃, OCH₂ CH₃, CN, CH₂ CH₂Cl, CH₂ CH₂ CH₂ Cl, CH₂ CH₂ OCH₃, OCH₂ OCH₃, CH₂ OCH₃, OCH₂ CH₂ OCH₃,CH₂ CO₂ R⁶, CH₂ CH₂ CO₂ R⁶, CO₂ R⁶, ##STR185## or NO; R⁶ is CH₃ or CH₂CH₃ ; and their agriculturally suitable salt.
 2. The compound of claim1,2-chloro-N-[(5-chloropyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide.3. A composition for the control on undesirable vegetation consistingessentially of an effective amount of a compound of claim 2 and at leastone of (a) a surface-active agent and (b) a solid or liquid diluent. 4.A composition for the control of undesirable vegetation consistingessentially of an effective amount of a compound of claim 1 and at leastone of (a) a surface-active agent and (b) a solid or liquid diluent. 5.A method for the control of undesirable vegetation comprising applyingto the locus of such undesirable vegetation a herbicidally effectiveamount of a compound of claim 1.